Phone book publisher Dex Media (NASDAQ:DXM) has filed for bankruptcy protection after reaching a restructuring deal with creditors.

The Chapter 11 announcement marks the fifth time in seven years the firm or its predecessors have found themselves in a bankruptcy court as yellow-pages companies struggle with the move of advertisers to the Internet.

Dex Media reported $1.27B in assets and $2.65B in debts as of Dec. 31.

Phone book publisher turned speculative investment Dex Media (OTCPK:DXMM) is preparing its third bankruptcy in seven years, The Wall Street Journal reports.

That's a delay from a filing that was expected to come in December. Stock fell 60% on OTC markets this afternoon to $0.08/share; it was delisted by Nasdaq in January after losing the bulk of its value.

With a market cap of about $1.4M, the company has reportedly reached a deal with key creditors to cut its debt by more than $1B with a prepackaged Chapter 11 filing to come next month. The company had $175M in cash as of the end of 2015.

Struggling yellow-pages publisher (and now penny stock) Dex Media (NASDAQ:DXM) is up 10.2% after filing that it's gotten yet another amendment to its forbearance deal from creditors.

The last expiration date, set for midnight last night, has been extended to 11:59 p.m. on Jan. 18. Without written notice, however, that date can be extended to five days after such notice is received.

The company is headed to pink sheets from Nasdaq likely by Thursday's market open, as Nasdaq intends to suspend trading then, and Dex says it doesn't intend to appeal that decision.

With the expiration of a grace period for a missed debt payment, Moody's has downgraded Dex Media's (DXM-3%) Probability of Default Rating, saying that the company has defaulted on the debt in its definition.

Further downgrades could come, the firm says, if Dex defaults on other elements, executes a distressed exchange or pursues reorganization in bankruptcy.

The company justified the downgrade pointing to its high leverage, the "rapid structural decline" in print directories, and increased competition and low barriers to entry in digital advertising, where Dex is "very weakly positioned and executing poorly."

Dex Media skipped an interest payment on Sept. 30, signed a forbearance deal with senior lenders, and got another forbearance extension until 11:59 p.m. Monday night.

It's been widely thought to have been pursuing a prepackaged bankruptcy to be filed by mid-December (about now).

Dex Media (DXM-4%) is nearing a deal with its creditors that would mean its third bankruptcy in seven years, Bloomberg reports.

The company is finalizing a prepackaged Chapter 11 filing for December to manage its $2.3B in debt. It's working with senior lenders on the deal but will seek broader support before a likely filing in the second week of December.

After the company skipped its Sept. 30 interest payment (and officially defaulted on it a month later), junior creditors had considered putting the company into involuntary bankruptcy. Junior support would also dictate time in bankruptcy if the company files for Chapter 11 voluntarily.

Aside from missing a payment on subordinated debt, Dex is also in default on its four term loans, though it has an agreement for forbearance through Nov. 23.

The company was forged from bankruptcies: The former R.H. Donnellley came out of Chapter 11 in 2010 as Dex One, which then chose to combine with emerging-from-bankruptcy SuperMedia. The companies filed again in 2013 to wrap their merger.

Struggling Dex Media (NASDAQ:DXM) is up 3.4% as it's sealed a forbearance agreement with senior lenders good through Nov. 23, and says it's gotten a term sheet and restructuring support agreement from the lender committee.

"Constructive discussions" have led to the agreements, says CEO Joe Walsh. The company is continuing negotiations with the goal of a consensual restructuring.

The company had skipped an interest payment on more than $260M in debt on Sept. 30, and had a 30-day grace period to make that payment up. But it went into default when the end of October came without the payment as well.

Dex claims a strong liquidity position with $205.3M in cash, and that it expects no disruption to operations.

Dex Media (NASDAQ:DXM) -- trading slightly up most of the day -- tanked in the last 15 minutes to close down 36%, as a group of junior bondholders is demanding a meeting following the company's missed payment last week.

The company skipped an interest payment due Sept. 30 on more than $260M in debt. It's not technically in default until Oct. 30.

The junior creditors made the case in a letter to the company that it would need their support for consensual debt restructuring if it elects to file for bankruptcy. The group is also considering filing an involuntary bankruptcy petition after what it says have been months of unsuccessfully trying to negotiate with Dex.

Dex Media says it's negotiating with senior lenders over a possible restructuring of $2B in debt.

Dex Media (NASDAQ:DXM) is down another 11.4% to a new low as it skipped a payment due today on more than $260M in debt.

Senior lenders have come together (along with Houlihan Lokey) to talk about a restructuring of more than $2B in debt, the company says. It paid down more than $100M of that with cash in the first half.

Dex has until Oct. 30 to make today's missed payment before it's in default. The company's 8-K says it has $251M in cash on hand, which it sees as "substantial liquidity" to fund operations.

Dex Media (NASDAQ:DXM) has promoted James McCusker to the post of chief revenue officer, restocking a role that has been the subject of some reshuffling this year.

McCusker, previously the VP of expansion channel sales, takes responsibility for a 1,700-person sales force and all aspects of sales strategy, planning, recruiting, training an execution. He has more than 23 years of experience in the field, and joined the company in May from hibu (the former Yellowbook).

Chief Revenue Officer Delbert Humenik resigned in May, six months after taking the role in a November reorganization.

With another late fall-off, Dex Media (NASDAQ:DXM) is sinking yet again, -22.8% in the wake of this morning's earnings, where revenues fell another 18% Y/Y and it posted net losses of $42M, bringing the YTD loss to $101M.

Print ad sales (down 22.8%) and digital ad sales (down 22.1%) contributed fairly equally to the sales decline. The spring has meant turmoil in the sales organization after its chief revenue officer resigned in early May.

The company's under a delisting threat after Nasdaq gave it 180 days to reach and hold $15M in market value. Dex's market cap has fallen to $6.3M today.